Your well-intentioned anonymous love note to an unrequited crush wasn’t going to make anyone swoon last Valentine’s Day, and it still won’t this year. Maybe you think sending an affectionate, cryptic letter is going to get the wheels turning in the recipient’s head, prompting hope that there’s someone out there (you) destined to sweep them off their feet, but unfortunately, you may want to forget all that. Love in our and day and age doesn’t follow a storybook script, if it ever did at all, and there’s reasons why an anonymous love note, bouquet, or box of chocolates can land with a thud in someone’s trashcan.
It can be seen as immature
It’s one thing when you’re in third grade and feel bashful about telling someone you like them, but it’s another when you’re an adult who presents the emotional maturity of a bashful third grader. If you’re serious about starting a relationship—even if you just want to test the waters—it’s best to be direct. Skirting around your feelings doesn’t suggest that you’ll necessarily be an emotional bedrock in a relationship.
You also have to ask yourself what the point of obscuring your identity might be. Is it because the person you’re professing love for is in a relationship and you don’t want to help drive a wedge through it, even though you are? Are you trying to trick them into liking you by having them feel the flutter of a gift, and then pairing yourself to it after? You’re not really doing anyone a favor by signing an anonymous love letter on Valentine’s Day.
It can be seen as creepy (especially for women)
As it happens in movies, an anonymous rose might work wonders if sent to a woman trapped in a loveless marriage. Perhaps the sender seems to really understand said woman, while her husband could care less. There’s a reason it’s a pop-cultural trope: Because it rarely, if ever, pans out that way.
If you’re a man, you also have to consider that a woman might read an anonymous note and worry that she’s being stalked. It’s a sad reality that predators exist, and it’s probably a cold comfort knowing that whoever sent you a care package might not truly have the best intentions in mind.
You can be mistaken for someone else
How much room for a total backfire would you like to allow? In one of of several possible disaster scenarios, the object of your affection could wrongfully assume your missive was sent by someone else. And what if your crush seeks that person out? It stands to reason that if you intentionally omit your name, your affections can go unrecognized, and who really benefits from that?
All of this is to say that you should feel comfortable sending someone a love note or gift this Valentine’s Day, just make sure it also comes with full transparency of who the gift is from.